Synthesis and Biological Activity of Guanylhydrazones of 2- and 4-Pyridine and 4-Quinoline Carboxaldehydes

Foye, William O.; Almassian, Bijan; Eisenberg, Marc S.; Maher, Timothy J.

doi:10.1002/jps.2600790615

Cited by 16 publications

(10 citation statements)

References 5 publications

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Compound 3 is a new unpublished agent. Compounds 4-10 have been described in the literature 11,12,32,33 , but never for their application in AChE inhibition or reactivation, and thus, this is a new type of application for guanylhydrazones.…”

Section: Synthetic Aspectsmentioning

confidence: 99%

Design, synthesis, and evaluation of guanylhydrazones as potential inhibitors or reactivators of acetylcholinesterase

Petronilho

Rennó

Castro

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

View full text Add to dashboard Cite

Analogs of pralidoxime, which is a commercial antidote for intoxication from neurotoxic organophosphorus compounds, were designed, synthesized, characterized, and tested as potential inhibitors or reactivators of acetylcholinesterase (AChE) using the Ellman's test, nuclear magnetic resonance, and molecular modeling. These analogs include 1-methylpyridine-2-carboxaldehyde hydrazone, 1-methylpyridine-2-carboxaldehyde guanylhydrazone, and six other guanylhydrazones obtained from different benzaldehydes. The results indicate that all compounds are weak AChE reactivators but relatively good AChE inhibitors. The most effective AChE inhibitor discovered was the guanylhydrazone derived from 2,4-dinitrobenzaldehyde and was compared with tacrine, displaying similar activity to this reference material. These results indicate that guanylhydrazones as well as future similar derivatives may function as drugs for the treatment of Alzheimer's disease.

show abstract

Section: Synthetic Aspectsmentioning

confidence: 99%

Design, synthesis, and evaluation of guanylhydrazones as potential inhibitors or reactivators of acetylcholinesterase

Petronilho

Rennó

Castro

et al. 2015

Journal of Enzyme Inhibition and Medicinal Chemistry

View full text Add to dashboard Cite

show abstract

“…1). The guanylhydrazones represent a class of compounds that presents a great variety of biological activity, and have been successfully used as antihypertensive, 31 …”

Section: -15mentioning

confidence: 99%

A new guanylhydrazone derivative as a potential acetylcholinesterase inhibitor for Alzheimer's disease: synthesis, molecular docking, biological evaluation and kinetic studies by nuclear magnetic resonance

et al. 2017

View full text Add to dashboard Cite

show abstract

“…There are several reports of guanylhydrazones being studied as antihypertensives [9,10], antidiabetic [11,12], antitumor [8,9], antibacterial [3,13,14], antimalarials [15], and trypanocidal [6,16,17].…”

Section: Introductionmentioning

confidence: 99%

Thermal characterization of some guanylhydrazones by thermal and nonthermal techniques

galvão

Brito

Dantas

et al. 2014

J Therm Anal Calorim

View full text Add to dashboard Cite

2-[(3,5-di-tert-butyl-4-hydroxyphenyl)methylene]-hydrazinecarboximidamide (WE010), 2-([1,1 0 -biphenyl]-4-ylmethylene)-hydrazinecarboximidamide (WE014), and 2-[(3,4-dichlorophenyl)methylene]-hydrazinecarboximidamide (WE017) are guanylhydrazone derivatives widely studied biologically and chemically; however, there are no studies regarding their thermal behaviors. The present study aims to apply the thermal analyses: differential scanning calorimetry (DSC), differential scanning calorimetry coupled to the photovisual system (DSC-photovisual), and thermogravimetry (TG), to characterize the guanylhydrazones, as well as HPLC and FTIR. The DSC curve of WE010 shows a melting process with T onset at 190°C and peak at 193.5°C (DH 41.0 J g -1 ). Due to the symmetry of the melting peaks obtained by DSC, it is possible to calculate the purity of the sample (98.87 %). The DSC curve of WE014 shows the melting process in the range of 208-213°C, with a melting peak at 211°C (DH 61 J g -1 ).The DSC curve of WE017 showed T onset at 215°C and peak temperature of 219°C (DH 55 J g -1 ). The TG curve of WE010, WE014, and WE017 presents initial decomposition temperatures of 186.95, 197.31, and 195.44°C, respectively. The DSC-photovisual confirmed the results of DSC and TG. The HPLC determined the purities of the samples and confirmed the results of DSC. The FTIR confirmed the thermal data. Thus, the use of thermal analysis is an important tool for the characterization of molecules with therapeutic potential contributing to the characterization and evaluation of their stability as well as nonthermal technique with complementary tool.

show abstract

Synthesis and Biological Activity of Guanylhydrazones of 2- and 4-Pyridine and 4-Quinoline Carboxaldehydes

Cited by 16 publications

References 5 publications

Design, synthesis, and evaluation of guanylhydrazones as potential inhibitors or reactivators of acetylcholinesterase

Design, synthesis, and evaluation of guanylhydrazones as potential inhibitors or reactivators of acetylcholinesterase

A new guanylhydrazone derivative as a potential acetylcholinesterase inhibitor for Alzheimer's disease: synthesis, molecular docking, biological evaluation and kinetic studies by nuclear magnetic resonance

Thermal characterization of some guanylhydrazones by thermal and nonthermal techniques

Contact Info

Product

Resources

About